European Journal of Organic Chemistry

thumbnail image: European Journal of Organic Chemistry
  • Editorial Board: Burkhard König, Universität Regensburg (Chairman of the Editorial Board)
  • Published Date: 01 January 1998
  • Source / Publisher: Wiley-VCH & ChemPubSoc Europe
  • Associated Societies: ChemPubSoc Europe

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The European Journal of Organic Chemistry (2016 ISI Impact Factor: 2.834) publishes Full Papers, Communications, and Microreviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry.


EurJOC is published on behalf of ChemPubSoc Europe, an organization of 16 European chemical societies. It is a sister journal of the Asian Journal of Organic Chemistry (AsianJOC) and is supported by the Asian Chemical Editorial Society (ACES).


The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:


 

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nadia dawoud wrote:

Synthesis of Some New Annulated Thieno Pyridine,Pyrazolopyridine and Pyrido Pyridine Derivatives

Abstract The reaction of arylidenemalonitrile with cyanothioacetamide afforded pyridine derivatives. Thus compound 1 reacted further with different nucleophilic and electrophilic reagents yielding different products which were confirmed via spectroscopic analysis. Keywords: Arylidene malononitriles,Dihydropyridines,Antimicrobial activity. Introduction No doubt that thienopyridines are an interesting class of heterocycles and their chemistry has recently received considerable attention especially because of their potential utility as antibacterial(1-4) antihypertensive(5), diabetes mellitus(6-8), as well as analgesics and antiinflammat,sedatives, anticougulants(9-11)), antiortherosclerotics(12) and as gondatropin releasing hormone antogeonsits(13). The derivatives of thiopyridines are also useful intermediates for the synthesis of some medicines and related compounds. It was discovered that the pyridyl thiolate moiety enhances antifungal and antiinflammatory activities of several important drugs (14, 15). Herein we report some new pyridinethione derivatives and their related product. Results and Discussion Thus pyridinethione derivative 1, which is prepared according to the literature (16, 17) was reacted with active methylene compounds namely,chloromalononitrile ,and/or ethylbromoacetate in refluxing pyridine to afford the theinopyridine derivatives (3a,b) respectively. The structure of compounds 3a,b was established based on the elemental analysis and spectral data. The mass spectrum of compound 3a is compatible with the molecular ion peak at m/z=229 (M+). Compound 3a is assumed to proceed via reaction of compound 1 with -halo compound to afford the S-alkylated derivative 2a followed by cyclization to 3a. The mass spectrum of compound 3b is compatible with the molecular ion peak at m/z = 276 (M+) (Scheme 1). Scheme (1) Alkylation of pyridinethione 1 with methyl iodide gave the S-methyl derivative 4 which was reacted with hydrazine hydrate to give the product 5 in a good yield (18,19). The IR spectrum of 5 showed the presence of absorption peak at 3412-3323cm–1 for two NH2 and 3280-3200 cm–1 for NH group respectively. The 1H-NMR spectrum of compound 5 exhibited a singlet at  11.64 ppm for NH group in addition to the signals of NH2 and CH3 in their proper positions. Accordingly this reaction product could be formulated as [3,6-d] amino pyrazolo[2,3-c]pyridine derivative (Scheme 2). Scheme 2 On the other hand, compound 1 was reacted with hydrazine hydrate in ethanolic solution to afford the pyridotriazine derivative 6. The structure of compound 6 was established based on its elemental analysis and spectral data. The mass spectrum of compound 6 showed the molecular ion peak at m/z = 216 (M+).The IR spectrum agreed well with the proposed structure. Also acetylation of the pyridine thione 1 with acetic anhydride afforded the acetyl derivative 7. The structure of compound 7 was confirmed by its correct elemental analysis and spectral data. The IR spectrum of compound 7 exhibited the disappearance of the absorption band due to the NH2 functional group at 3450-3300cm–1 and appearance of NH group at 3346-3181cm–1 and CO acetyl at 1717cm–1. The 1H-NMR of 7 revealed  2.50ppm (s, 3H,CH3), 3.73ppm (s, 3H,COCH3), 12.78ppm (br, 1H). Also, the mass spectrum of compound 7 was compatible with the molecular formula C10H8N4OS at m/z = 232 (M+) (Scheme 3). Scheme 3 Also, the reaction of compound 1 w¬ith acrylonitile afforded the N-ethylcyano derivative 8. The 1H-NMR spectrum of compound 8 revealed the structure of this compound. The mass spectrum of compound 8 is compatible with the molecular ion peak at m/z = 274 (M+) corresponding to the molecular formula C11H9N¬5S. Furthermore, compound 8 was reacted with aryl cinnamonitrile derivatives 9a-d to afford product of condensation which was formulated as structure 10a,d with the elimination of hydrogen cyanide .Structure 10a-d was established based on 1H-NMR that revealed the presence of ethyl function in the reaction product (Scheme 4). Scheme (4) Similarly the pyridinethione (1) reacted with arylidine malononitrile 9a-d in boiling pyridine to afford the pyridopyridine derivatives 11a-d. The structures of compounds (11a-d) were confirmed by elemental analysis and spectroscopic data. The IR spectrum of compound 11a showed the presence of absorption peaks at 3319cm–1 for vNH2, 1630cm–1 for vC=N and 1210cm–1 for vC=S functional groups. The 1H-NMR spectrum of 11a exhibited signals at  3.44 ppm for NH2 group in addition to the aromatic protons. Also the mass spectrum of compound 11b showed a molecular ion peak at m/z = 347 (M+) corresponding to the molecular formula C18H13N5OS. In a similar manner, the reaction of 1 with malononitrile and formaldehyde, and/or acetaldehyde yielded the corresponding 2-thioxopyridopyridine derivatives 12a,b respectively. The structure of compounds 11and 12 were confirmed by elemental analysis and spectroscopic data (Scheme 5). Scheme 5 The thienopyridine derivative 13 was readily obtained via the reaction of compound 1 with elemental sulphur. Subsequent treatment of compound 13 with acrylonitrile resulted only in cyanotheylation product 14. Compounds 13 and 14 were confirmed by elemental analysis and spectroscopic data. (Scheme 6). Scheme 6 Experimental Melting points were taken with the help of stuart apparatus and were uncorrected.The IR spectra were produced with a Jasco FT/IR 5300 spectrophotometer using the KBr technique.1H–NMR spectra were measured using a Jeol FX-100 spectrometer 60 MHz and a Varian Gemini 200 instrument 200 MHz and 250 & 300 MHz with TMS as an internal reference. Mass spectra were obtained by using of a Schimadzu-GC MS-QP 1000 EX instrument using the direct inlet system Microanalyses were performed by the microanalytical unit at Cairo University. All compounds gave satisfactory elemental analyses. Synthesis of 6-Amino-4-methyl-6-thioxo-1,2-dihyropyridine-3,5-dicarbonitrile (1). It was prepared according to the literature. The mass spectrum of (1) exhibited a molecular ion peak at m/z (160, 100%). 1HNMR spectrum of (1) exhibited signals at δ 1.21 (3H, s,3H,CH3) 3.34 (2H,s,2H,NH2), 12.76 (br,1H,cyclic NH). Synthesis of 3,6-Diamino-4-methylthieno [2,3-b] pyridine-2,5-dicarbonitrile (3a). A mixture of (1) (0.01 mol) and chloroacetonitrile (0.01 mol) in 15ml of pyridine was refluxed for 5h, after cooling the obtained product it was recrystallized from DMF to give (3a). MS of (3a). C10H7N5S, exhibited a molecular ion peak at m/z 229 (M+, 100%). 1H-NMR spectrum of (3a) exhibited signals at δ 2.50 (3H, s,3H,CH3), 3.33 (2H, s2H,NH2), 4.29 (2H, s,2H,NH2). Synthesis of 3,6-Diamino-5-cyano-2-ethoxy carbonyl-4-methyl thieno[2,3-b] pyridine(3b). A mixture of (1) (0.01 mol), ethylbromoacetate (0.01 mol) in 15 ml of pyridine was refluxed for 5h. The reaction mixture was then cooled and the obtained product was recrystallized from ethanol to give (3b). 1HNMR spectrum of (3b) exhibited signals at δ 1.21 (t,CH,CH2CH3), 4.15 (q,2H,CH2,CH3), 3.32 (s,3H,CH3). Synthesis of 2-Amino-4-methyl-6-thioxomethyl pyridine-3,5-dicarbonitrile (4). A mixture of 1 (0.01 mol) andmethyl iodide (0.01 mol) in 20 ml of dry acetone in the presence of anhydrous potassium carbonate (0.5g) was refluxed for 4h. The reaction mixture was then cooled poured into a beaker containing crushed ice (50 gm). The obtained product was recrystallized from ethanol to give (4). MS of (4) C9H8N4S exhibited a molecular ion peak at m/z (204, 100%). 1HNMR spectrum of (4) exhibited signals at δ 2.56 (s,3H,CH3), 3.61 (s,3H, S-CH3), 3.74 (s2H, NH2). Synthesis of 3,6-Diamino-4-methyl-1H-pyrazol [3,4-b] pyridine-5-carbonitrile (5). A mixture of (4) (0.01 mol) with and hydrazine hydrate (0.01mol) was refluxed for 4h. The obtained product was recrystallized from ethanol to give (5). MS of (5) C8H8N6 exhibited a molecular ion peak at m/z (188, 100%). 1H-NMR spectrum of (5) exhibited signals at δ 2.73 (s, 3H,CH3), 5.19 (s,2H,NH2), 6.54 (s, 2H,NH2) ,11. 64 (s,1H,NH cyclic). Synthesis of 4-Amino-5-methyl-7-thioxo-7,8-dihydropyrido [2,3-d] [1,2,4] triazine-6-carbonitrile (6). A mixture of (1) (0.01 mol) and hydrazine hydrate (0.01 mol), in ethanol (20 ml) was refluxed for 4h.The reaction mixture was then cooled and the obtained product was recrystallized from ethanol to give (6). MS of (6) C8H6N6S exhibited a molecular ion peak at m/z 218 (M-2], 25, 9%). 1H-NMR spectrum of (6) exhibited signals at δ 2.74 (s, 3H, CH3), 3.33 (s, 2H, NH2), 12.80 (s, 1H, NH cyclic). Synthesis of N-(3, 5-Dicyano-4-methyl-6-thioxo-1, 6-dihydro- Pyridine -2-yl) acetamide (7). A mixture of 1 (0.01 mol) and acetic anhydride (0.01 mol) was heated on a steam bath for 4hr. the reaction mixture was then cooled and the obtained product was recrystallized from DMF to give(7).MS of (7)C10H8N4OS exhibited a molecular ion peak at m/z 232 (M+, 26%). 1H-NMR spectrum of(7)exhibited signals at δ 2.50 (s,3H,CH3), 3.73 (s,3H,COCH3), 12.78 (br,1 H,cyclic NH). Synthesis of 6-Amino-1-(2-cyanoethyl)-4-methyl-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile (8). A mixture of (1) (0.01 mol), and acrylonitrile (0.01 mol) in pyridine (15 ml) was refluxed for 4h. The reaction mixture was then cooled,poured into ice-HCl mixture and the obtained product was recrystallized from ethanol to give (8). MS of (8) C11H9N5S exhibited a molecular ion peak at m/z (243, 24.7%). 1H-NMR spectrum exhibited signals at 2.52 (s,3H,CH3) 2.99 (q,2H-NCH2), 3.48 (q,2H,CH2CN), 3.41 (s,2H,NH2). Synthesis of 5-Amino-7-aryl-1-(2-cyanoethyl)-4-methyl-2-thioxo-1,2-dihydro[1,8] nphthydrine-3,6-dicrabonitrile (10a-d). A mixture of (8), (0.01 mol) and derivatives of malonitrile namely benzylidene malono nitrile,4-methoxy benzylidene and 4-chloro benzylidene (9a-d) (0.01 mol) in pyridine (20 ml) was refluxed for 8h. The reaction mixture was then cooled poured into container of crushed ice (50 gm), neutralized with dil. HCl (5 ml) and the obtained products were recrystallized from ethanol to give (10a-d). MS of (10a) C20H14N6S exhibited a molecular ion peak at m/z 370 (M+, 19.5%).1H-NMR spectrum of (10b) exhibited signals at δ 2.43 (s,3H,CH3), 2.99 (t,2H,CH2-N), 3.44 (t,2H,CH2CN), 3.34 (s,2H,NH2).1H-NMR spectrum of (10d) exhibited signals at δ 2.51 (s,3H,CH3), 3.01 (t,2H,N-CH2), 3.47 (t,2H,CH2CN), 3.28 (s,2H,NH2). Synthesis of 5-Amino-7-aryl-4-methyl-2-thioxo-1,2-dihydro-[1,8] naphthylridine-3,6-dicarbonitriles (11a-d). A mixture of 1 (0.01 mol), substituted arylidene derivatives of malononitrile (0.01 mol) in pyridine (20 ml) was refluxed 10h. The reaction mixture was then cooled poured into ccontainer of crushed ice, neutralized with dil. HCl (5 ml) and the obtained product was recrystallized from ethanol to give 11a-d. MS of 11a C17H11N5S exhibited as molecular ion peak at m/z (317, 100%). 1HNMR spectrum of 11b exhibited signals at 1.07 (3H, s), 2.11 (3H, s), 3.44(2H, s,) 7,19-8.03 (4H, m) 12.41 (1H, s), 1H-NMR spectrum of 11c exhibited signals at δ 1.21 (3H, t), 2.90 (2H, q), 3.36 (2H, s), 7.37- 7.67 (4H, m), 11.05 (1H, s). Synthesis of 5-Amino-4-methyl-2-thioxo-1,2-dihydro-1,8,naphthopyridine 3,6-dicarbonitriles (12a,b) . A mixture of 1 (0.01 mol), aliphatic aldehydes namely acetaldehyde and formaldehyde (0.01 mol) in 20 ml of alcohol in the presence of TEA was refluxed for 10h. The reaction mixture was then cooled and the obtained product was recrystallized from ethanol to give 12a,b. MS of 12b C12H9N5S exhibited a molecular ion peak at m/z = 253 (M+, 7%), 1H-NMR spectrum of 12a exhibited signals at δ 2.74 (3H,s), 4.69 (2H, s), 7.96 (1H, s), 8.68 (5H, s), 12.31 (1H, s). 1H-NMR spectrum of 12b exhibited 2.74 (3H, s), 2.90 (3H,s), 3.34(2H,s), 7.94(SH, s), 12.05 (1H, br). Synthesis of 3,6-Diamino-4-thioxo-4,5-dihydrothieno [3,4-c] pyridine-7-carbonitrile (13) A mixture of 1 (0.01 mol), and sulphur (0.01 mol) in 20 ml of alcohol/TEA was refluxed for 4h. The reaction mixture was then cooled and the obtained product was recrystallized from ethanol to give 13. MS of 13 C8H6N4S2 exhibited a molecular ion peak at m/z 220 (M+, 2.9%). Synthesis of 3,6-Diamino-5-(2-cyanoethyl)-4-thioxo-4,5-dihyro-thieno[3,4-c]pyridine-7-carbonitrile (14) A mixture of 13 (0.01 mol) and acrylonitrile (0.01mol), in 15 ml of pyridine was refluxed for 5h. The reaction mixture was then cooled and the obtained product was recrystallized from DMF to give 14. MS of 14 C11H9N5S2 exhibited a molecular ion peak at m/z 275 (M+, 11%). 1H-NMR spectrum exhibited signals at  2.98 (2H, q), 3.48 (2H, q), 3.01 (4H, br), 7.86 (1H, s), 7.97 (5H, br). Table (1) IR spectra of synthesized compounds Compd. No. max (cm–1) 1 3485(NH2), 3283(NH), 2989 (CH–arom.), 2924(CH aliph.), 2214(CN), 1639 (C=C), 1269 (C=S). 3a 3326, 2225 (NH2), 2978 (CH-arom.), 2926 (CH-aliph.), 2217(CN), 1629 (C=N), 1561 (C=C). 3b 3329, 3331 (NH2), 3013 (CH-arom.), 2979 (CH-aliph), 2210 (CN), 1731 (C=O), 1634 (C=N), 1558(C=C). 4 3409-3345(NH2), 2924(CH–arom.), 2920(CH aliph.), 2216(CN), 1673 (C=N), 1649 (C=C). 5 3412, 3323(2NH2), 3229(NH), 2207 (CN). 6 3362 (NH2), 3196(NH), 2974 (CH-arom.), 2936 (CH-aliph.), 2212(CN), 1643(C=N), 1599 (C=C), 1242 (C=S). 7 3317, 3220(NH), 3100(CH-arom.), 2980 (CH-aliph.), 2222(CN), 1736 (C=O), 1636 (C=C), 1272 (C=S). 8 3321, 3223 (NH2), 2979 (CH-arom.), 2947 (CH-aliph.), 2217 (CN), 1646 (C=C), 1267 (C=S). 10a 3388, 3322(NH2), 2980(CH-arom.), 2943 (CH-aliph.) 2223 (CN), 1698(C=N), 1652 (C=C), 1269 (C=S). 10b 3399, 3330(NH2), 2983(CH-arom., 2931 (CH-aliph.), 2224 (CN), 1648 (C=N), 1563 (C=C), 1270 (C=S). 10c 3385, 3325(NH2), 2980(CH-arom.), 2946(CH-aliph.), 2220 (CN), 1647 (C=N), 1563 (C=C), 1238(C=S). 10d 3323, 3226(NH2), 2980(CH-arom.), 2947 (CH-aliph.), 2219 (CN), 1648 (C=N), 1564 (C=C), 1269(C=S). 11a 3316(NH2), 3215(NH), 2917 (CH-arom.), 2849 (CH-aliph.), 2215(CN), 1626(C=N), 1561(C=C), 1242(C=S). 11b 3339(NH2), 3210(NH), 2919 (CH-arom.), 2844(CH-aliph.), 2214(CN), 1556(C=C), 1256 (C=S). 11c 3464(NH2), 3195(NH), 2973(CH-arom.), 3933(CH-aliph.), 2212 (CN), 1638 (C=N), 1598 (C=C), 1240(C=S). 11d 3317(NH2), 3191(NH), 2921(CH, arom.), 2900 (CH, Aliph.), 2213(C), 1635(C=N), 1566(C=C), 1271(C=S) 12a 3326(NH2), 3120(NH), 2927 (CH-arom.), 3050(CH-aliph), 2211 (CN), 1671 (C=N), 1629 (C=C), 1267 (C=S). 12b 3345(NH2), 3224(NH), 2974 (CH-arom.), 2923(CH-aliph.), 2214 (CN), 1626(C=N) 1563 (C=C), 1248 (C=S). 13 3375, 3310 (NH2), 3194(NH), 3020(CH-arom.) 2974(CH-aliph.), 2214(CN), 1636 (C=C), 1250 (C=S). 14 3426, 3324(NH2), 2979(CH-arom.), 2946(CH-aliph.), 2212(C–N), 1647(C=C), 1269 (C=S). Table (2) Physical and analytical data of the synthesized compounds Elemental analyses Calcd/Found(%) C H N S 1 72 210 ethanol C8H6N4S (190.23) 50.51 50.33 3.18 3.15 29.45 29.33 16.86 16.99 3a 69 256 Ethanol C10H7N5S (229.26) 52.39 54.21 3.08 3.12 30.53 30.61 13.99 13.69 3b 68 178 Ethanol C12H12N4O2S (276.32) 52.16 52.96 4.38 4.74 20.28 20.34 11.60 11.41 4 82 249 ethanol C9H8N4S (204.25) 52.92 52.90 3.95 3.64 27.43 27.34 15.70 15.62 5 89 190 ethanol C8H8N6 (188.15) 51.06 51.29 4.3 5.1 44.67 45.19 -- -- 6 91 >300 DMF C8H6N6S (218.24) 44.03 44.43 2.77 2.13 38.51 38.42 14.69 14.93 7 85 260 DMF C10H8N4OS (232.26) 51.71 51.67 3.47 3.21 24.12 24.00 13.81 13.91 8 82 262 ethanol C11H9N5S (243.29) 54.30 54.33 3.73 3.81 28.79 28.86 13.18 13.21 10a 69 275 ethanol C20H14N6S (370.43) 64.85 64.59 3.81 4.40 22.69 22.32 8.66 8.93 10b 64 277 ethanol C21H18N6OS (400.46) 62.98 62.19 4.03 4.93 20.99 20.80 8.01 8.09 10c 61 278 ethanol C20H13N6S (404.88) 59.33 59.10 3.24 3.79 20.76 20.77 7.92 7.43 10d 58 274 ethanol C19H13N7S (371.42) 61.44 61.22 3.53 3.39 26.40 26.00 8.63 8.34 11a 75 250 ethanol C17H11N5S (317.37) 64.34 64.01 3.49 3.21 22.07 22.87 10.10 10.32 11b 74 286 ethanol C18H13N5S (347.39) 62.23 62.54 3.77 3.05 20.16 20.76 9.23 9.44 11c 74 >300 ethanol C17H10ClN5S (351.81) 58.04 58.19 2.86 2.44 19.91 19.53 9.11 9.43 11d 75 >300 DMF C16H10N6S (318.36) 60.36 60.57 3.17 3.33 26.40 26.95 10.07 10.05 12a 87 >300 DMF C11H7N5S (241.27) 54.76 54.38 2.92 2.99 29.03 29.54 13.29 13.48 12b 86 >300 ethanol C12H9N5S (255.30) 56.45 56.38 3.55 3.91 27.43 27.16 12.56 12.47 13 78 294 Ethanol C8H6N4S2 (222.29) 43.22 43.01 2.72 2.81 25.20 25.98 28.85 28.09 14 72 >300 DMF C11H9N5S2 (275.36) 74.98 74.32 3.29 3.09 25.43 25.59 23.29 23.64 Antimicrobial Activity The newly synthesized compounds were screened for their antibacterial activity against two species of Gram positive bacteria, namely Bacillus subtilis and Staphylococcus aureus and two species of Gram-negative bacteria Escherichia coli and Pseudomonas aeruginos (Table 3). (In nutrient agar broth) and antifungal activity (in Dox’s medium and saboured’s agar) by the agar diffusion method (20,21) at a concentration 20 mg/ml using DMSO as solvent and blank. The compounds were tested also for their activities against antifungal such as Candida alicans and Candida parapsilosis (Table 4). The antimicrobial screening results were measured by the average diameter of the inhibition zones, expressed in mm. As shown in the results, all tested compounds displayed significant activities against bacteria, while compounds 1 and 13 were very active against all the tested organisms among all the tested compounds. Table (3): Antibacterial activity of synthesized compounds Compd. No Bacillus subtilis Staphylococcus aureus Escherichia coli Pseudomonas aeruginos 1 ++ +++ ++ +++ 3a ++ ++ ++ ++ 5 + + +++ + 6 ++ ++ ++ ++ 7 ++ ++ ++ ++ 8 + + – ++ 10a ++ ++ ++ ++ 10b ++ ++ ++ ++ 10c ++ + ++ ++ 11 ++ ++ ++ ++ 12 ++ ++ ++ ++ 13 ++ +++ ++ ++ Table (4): Antifungal activity of synthesized compounds Compd. No Candida albicans Candida parapsilosis 3a + + 6 + + 7 ++ ++ 8 + + 10a ++ ++ 10b ++ ++ 10c + + 11a + + 12 ++ ++ 13 ++ ++ The present investigation deals with the preparation of thienopyridine derivatives, these compounds are at least as effective as asprine in preventing vascular events in patients at high risk, and possibly somewhat more(22,23). One of the major classes of adenosine diphosphate (ADP) receptor antagonists are thienopyridines. Thienopyridines composes a subcategory of antiplatelet medication, known as receptor inhibitors, used commonly for the treatment of atherosclerotic cardiovascular disease (24). The thienopyridines derivatives play an important role in antibacterial and anticancer chemotherapy. As shown in the results (Table 5) most of compounds displayed activity as antitumors(25). Table (5): Antitumor activity of some prepared compounds % inhibition of cell viability (g/m) 100 500 25 1 35 5 0 3a 20 0 0 3b 30 10 0 10a 10 0 0 10b 50 20 0 11a 30 10 0 11b 70 35 0 11c 60 30 5 12 60 30 10 References 1. W. Gobel, Pharmazie, 29, 744 (1974). 2. J.C. Black and D. Howes, Toxicology. Annual, 3,1 (1979). 3. M. Nakanish, H. Imamara, Y. Marayama, and Hivosuki, Chem. Abst. 90, 272 (1970); Chem. Abst., 90, 54504 (1970). 4. Z. Shraideh and A.K. Salla, Bimed. Lett., 54, 233 (1997). 5. P.M. Gilis, A. Haemera, and W. Bollaerto Eur. J. Med. Chem., 15, 185 (1980). 6. Mongevega, A., Aldama, I., Robbani, M.M.; Femandez Alverez, E. J. Heterocycl. Chem. 17,77, (1980). 7. Bellary, J. H.; Badiger, V.V. Indian J. Chem. 20B 654 (1981). 8. Joshi, K.C. Chand, P.; Heterocylce. 17, 1783 (1980). 9. Yossef, M.S.K.; Hassan, KH. M.; Atta F.M.; Abbady, M.S. J. Heterocycle. Chem. 21, 1565 (1984). 10. Pottus, K.T.; Husain, S.J. Org. Chem. 10, 36(1971). 11. Bridson, P.K.; Davis, R.A.; Renuer, L.S. J. Heterocyl. Chem. 22, 753 (1985). 12. Saito, Y.; Yasushi, M., Sakoshita, M.; Toyda, K.; Shibazalti, T. European Appl.; 535, 548 (1993) Chem. Abstr., 119, 117112e (1993). 13. Furuga, S/; Takeru, N.; Matsumoto, H. Jpn. Kokai Tokkyo Koko JP 09, 169, 766 Chem. Abst., 127 176416v (1997). 14. Aronldi, A.; grasso, S., Meinardi, G., Merlini, L. Eur. J. Med. Chem. 23, 149 (1978). 15. Maciej J. Nowak, L. Lapinski, H. Rost. Kowska, A. Les and L. Adamowiez. J. Phys. Chem., 94(19), 7406-7414 (1990). 16. G. Elgemeie, M.Sallam, S.Sherief and M.H. Elnagdi J. Heterocycles, 23, 12 (1985). 17. A.E.Fedorov,A.M.Shestopalov,andP.A.Belyakov,Izv.Akad,Nauk,Ser.Khim.,2081(2003). 18. Sharma. P., Hussain. K.F., Sukhwal. S., Kothari. S., Singhal M. and verma. B. L.; Indian. J. Chem. Sect. B. 33B, 8, 966 (1999) Chem. Abst., 132, 207817m (2000). 19 - El– Assiery.A.S; Galal.H.S; Ahmed.F; Acta.Farm.54, 143-150 (2004). 20- Grayer, R.J.; Harborne, J.B. A survey of Antifungal compounds from higher plants. Photochemistry, 37, 19-42 (1994). 21- Irob, O.N.; Moo-Young, M.; Anderson, W.A. Antimicrobial activity of annatto extract. Int. J. Pharm. 34, 87-90 (1996). 22- Federico M. Goodsaid, J. Pharma cotherapy, 28(12), 1423-1424 (2008). 23- Hankey G.J, Sudlow CLM, Dunbabin DW. Oxford, UK: Stroke 31, 1779-1784 (2000). 24- M. Hashemzadeh, S. Goldsbery, M. Furukav, J. Invasive Cardiology, 21, 406-412 (2009). 25- I. Hayakawa; R. Shioya; T. Agatsuma; H. Furnkawa and Y. Sugano; Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure activity relationships. Bioorganic & Medicinal Chemistry Letters, 14, 3411-3414 (2004).

Wed Jun 08 10:50:40 UTC 2011

qiyin chen wrote:

an growing journal vs JOC

I like EJOC. It is growing very fast. All papers published on it are high quality and creative.

Sun Apr 17 20:54:23 UTC 2011

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